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| | Southland Oaks Winners | | | | | | | | |
| Year | Winner | Driver | Trainer | Track | Distance | Time | Sire | Second |
| 1 | 1983 | Jilaire Bogart | Henry Skinner | G S Hamilton | Invercargill | 2200m | 2.52.0 | Bogart Hanover | Ill Wind |
| 2 | 1984 | Josesphine Bret | Allan Beck | RJ Beck | Winton | 2400m | 3.04.8 | Knowing Bret | Timepiece |
| 3 | 1985 | Springfield Countess | Alan Scobie | GA Gibson-Smith | Gore | 2200m | 2.50.8 | Alba Counsel | Chipaluck |
| 4 | 1986 | Carefree Princess | Robin Swain | JP Kelly | Wyndham | 2400m | 3.04.8 | Pass with Care | Kates Reign |
| 5 | 1987 | Rapture | Russell Kerr | DM Kerr | Invercargill | 2200m | 2.51.8 | Son Of Afella | Girl George |
| 6 | 1988 | Scapa Chip | Colin Lee | EJ Lee | Winton | 2400m | 3.04.8 | Taurus Chip | Anna Patron |
| 7 | 1989 | Adrenalin | Allan Beck | JR Smith | Gore | 2200m | 2.51.8 | Surmo Hanover | Celebration |
| 8 | 1990 | Gypsy Winkle | Trevor Walsh | CJ Cliene | Wyndham | 2400m | 3.05.7 | Nero's BB | Bullet Ahead |
| 9 | 1991 | Star of Bethleham | Paul Kerr | PF Kerr | Invercargill | 2200m | 2.47.2 | Soky's Atom | Superior Miss |
| 10 | 1992 | Maude's Gift | Henderson Hunter | WO Hunter | Winton | 2400m | 3.08.7 | Preux Chevalier | Gandi's Pride |
| 11 | 1993 | Lento | Henry Skinner | HW Skinner | Gore | 2200m | 2.48.2 | People's Blue Chip | Meagunn |
| 12 | 1994 | Barossa | Robert Cameron | RM Cameron | Wyndham | 2400m | 3.04.6 | Andrel | Pretty Kiwi |
| 13 | 1995 | Lover's Wish | Kirk Larsen | BG Buchanan | Winton | 2400m | 3.06.4 | Son Of Afella | Beaudiene Debtor |
| 14 | 1996 | Impact | Ricky May | RL Tatterson | Wyndham | 2400m | 3.03.0 | Holmes Hanover | True Annette |
| 15 | 1997 | Mystic Gold | Jamie Keast | JT Keast | Winton | 2400m | 3.03.0 | Butler's BG | Spicy Atom |
| 16 | 1998 | Tartan Lady | Allan Beck | RJ Faithful | Invercargill | 2200m | 2.50.4 | Holmes Hanover | Shout the Girls |
| 17 | 1999 | Windermere Girl | Brent Barclay | MG Faul | Invercargill | 2200m | 2.41.6 | In The Pocket | OK Rock |
| 18 | 2000 | Flash Tactics | Ricky May | DP Dynes | Invercargill | 2200m | 2.43.6 | Soky's Atom | Memesis Choice |
| 19 | 2001 | Shortys Girl | Allan Beck | AR Beck | Invercargill | 2200m | 2.46.1 | New York Motoring | Sparks A Flyin |
| 20 | 2002 | Oaxaca Lass | Jim Curtin | NJ Hamilton | Invercargill | 2200m | 2.42.6 | Holmes Hanover | Whanau |
| 21 | 2003 | Champagne Princess | Jack Smolenski | JW Smolenski | Invercargill | 2200m | 2.44.2 | Soky's Atom | Precocious Title |
| 22 | 2004 | Nursemaid | Hamish Hunter | AFH Hunter | Invercargill | 2200m | 2.50.7 | Caprock | Hilarious Leigh |
| 23 | 2005 | Mainland Banner | Ricky May | RJ Dunn | Invercargill | 2200m | 2.49.6 | Christian Cullen | Rakalees |
| 24 | 2006 | Zitura | Clark Barron | KM Barron | Invercargill | 2200m | 2.43.1 | Union Guy | Holmezy |
| 25 | 2007 | Suvarno Hanover | Terry Chimel | JM Howe | Invercargill | 2200m | 2.43.4 | Holmes Hanover | Seafield Princess |
| 26 | 2008 | Kiwi Ingenuity | Robbie Holmes | R Holmes | Invercargill | 2200m | 2.41.5 | Christian Cullen | Badlands Jewel |
| 27 | 2009 | Beaudiene Bad Babe | Andrew Armour | M Brown | Invercargill | 2200m | 2.43.0 | Badlands Hanover | Pay Me Painter |
| 28 | 2010 | Royal Cee Cee | Michael House | M House | Invercargill | 2200m | 2.47.6 | Christian Cullen | Tres Bien Franco |
| 29 | 2011 | Jumpforjoy | Clark Barron | CJ Barron | Invercargill | 2200m | 2.42.8 | Bettor's Delight | Kristina |
| 30 | 2012 | Gaylee's Delight | Dexter Dunn | Greg and Nina Hope | Invercargill | 2200m | 2.41.1 | Bettor's Delight | Shezaball |
| 31 | 2013 | Safedra | Dexter Dunn | Cran Dalgety | Invercargill | 2200m | 2-47.7 | Mach Three | Justalittlebettor |
| 32 | 2014 | Royal Counsel | Gordon Lee | Colin and Gordon Lee | Invercargill | 2200m | 2-39.4 | Gotta Go Cullect | Raksdeal |
| 33 | 2015 | Smokin Bird | Jonny Cox | Kevin Court | Invercargill | 2700 m | 3-23.4 | Bettor's Delight | Donagal Kahlum |
| 34 | 2016 | Nek Time | Dexter Dunn | Terry and Glenys Chmiel | Invercargill | 2700 m | 3-19.4 | Gotta Go Cullect | Scarlett Falcon |
| 35 | 2017 | Bonnie Joan | Dexter Dunn | Cran Dalgety | Invercargill | 2700 m | 3-17.1 | Somebeachsomewhere | Delightful Memphis |
| 36 | 2018 | Dibaba | Terry Chimel | Terry and Glenys Chmiel | Invercargill | 2700 m | 3-26.9 | Shadow Play | Tres Vite |
| 37 | 2019 | Pressed For Time | John Dunn | Tom Bagrie | Invercargill | 2700 m | 3-25.0 | Sportswriter | Kendra |
| 38 | 2020 | Stylish Memphis | Ricky May | Mark Jones | Invercargill | 2700 m | 3-16.3 | Bettor's Delight | Need You Now |
| 39 | 2021 | Bettor Talk Art | Robbie Close | Regan Todd | Invercargill | 2700 m | 3-21.2 | Bettor's Delight | Lifes A Beach |
